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J Org Chem. 2006 Jul 7;71(14):5407-10.

Organocatalytic asymmetric deconjugative Michael additions.

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  • 1Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.


The organocatalytic allylic C-C bond-forming addition of activated alkylidenes to acrolein has been achieved with good yield and regio- and enantioselectivity. Chiral tertiary amines in the form of cinchona alkaloid catalysts are used to give allyl intermediates that exhibit unusual alpha-selectivity in the C-C bond-forming step. The products are transformed into a large range of intermediates that are difficult to access via alternative methods, using different oxidative and reductive protocols.

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